Why We Love It: Hidden in plain view, this tropical retreat straddles the Gulf Coast between Naples and Marco Islands. No bridges connect it to the mainland, so you’ll need to make like a local and go by boat.
Where To Stay: Both Naples and Marco are chock-a-block with fine resorts, but the Naples Bay Resort offers an affordable Boatel package. A waterfront hotel room plus a 22-foot bow rider for $369 (regular room rates from $229 with boat rental starting at $420). naplesbayresort.com or 866/605-1199
What To Eat: Pack a picnic if you like (be sure to bring plenty of cold drinks), but look to the Intracoastal around lunchtime for the local burger barge, which pulls up on the sand to serve hot sandwiches with ice-cold sodas and beer.
What To Do: Dock on the Intracoastal side for a glorious day of beachcombing, sunning, fishing, and strolling on a deserted isle.
Insider's Tip: The first weekend in May locals from Naples and Marco throw a beach party at Keewaydin, linking their boats around the south end of the island.